N2-isobutyryl-5-[2'-deoxy-β-D-threo-pentofuranosyl]-2-aminoquinazoline

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: N2-isobutyryl-5-[2'-deoxy-β-D-threo-pentofuranosyl]-2-aminoquinazoline
• 英文别名: N-[5-[(2R,4R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]quinazolin-2-yl]-2-methylpropanamide
• 化学式: C₁₇H₂₁N₃O₄
• 分子量: 331.371
• InChiKey: IESCIWNHCRFQKO-RBSFLKMASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N2-isobutyryl-5-[2'-deoxy-β-D-threo-pentofuranosyl]-2-aminoquinazoline 在 吡啶 、 4-二甲氨基吡啶 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 25.17h， 生成 N2-isobutyryl-5-[2'-deoxy-β-D-threo-pentofuranosyl-3'-O-(2-cyanoethoxy)(diisopropylamino)phosphino-5'-O-(4,4'-dimethoxytrityl)]-2-aminoquinazoline
  参考文献：
  名称：

  Design of Triple Helix Forming C-Glycoside Molecules

  摘要：

  The modeling, synthesis, and characterization of oligomers containing 2-aminoquinazolin-5-yl 2'-deoxynucleotide residues are reported. The 2-arninoquinazoline residues sequence specifically bind via Hoogsteen base pairing as a third strand in the center of the major groove at TA base pair Watson-Crick duplex sequences. Evidence for the formation of a sequence specific three-stranded structure is based on thermal denaturation UV-vis and fluorescence studies. The novel 2-aminoquinazoline C-nucleoticle is a component of a system designed to overcome the homopurine requirement for triple helix structures.

  DOI：

  10.1021/ja028033x
• 作为产物：
  描述：

  2-溴-6-硝基苄溴 在 吡啶 、 盐酸 、 三甲基氯硅烷 、 palladium bis(dibenzylideneacetone)palladium⁽⁰⁾ 、 三叔丁基膦 、 硫酸 、 四丁基氟化铵 、 三乙酰氧基硼氢化钠 、 铁粉 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 乙二醇乙醚 、 乙醇 、 乙腈 为溶剂， 反应 7.01h， 生成 N2-isobutyryl-5-[2'-deoxy-β-D-threo-pentofuranosyl]-2-aminoquinazoline
  参考文献：
  名称：

  Design of Triple Helix Forming C-Glycoside Molecules

  摘要：

  The modeling, synthesis, and characterization of oligomers containing 2-aminoquinazolin-5-yl 2'-deoxynucleotide residues are reported. The 2-arninoquinazoline residues sequence specifically bind via Hoogsteen base pairing as a third strand in the center of the major groove at TA base pair Watson-Crick duplex sequences. Evidence for the formation of a sequence specific three-stranded structure is based on thermal denaturation UV-vis and fluorescence studies. The novel 2-aminoquinazoline C-nucleoticle is a component of a system designed to overcome the homopurine requirement for triple helix structures.

  DOI：

  10.1021/ja028033x

文献信息

• Design of Triple Helix Forming C-Glycoside Molecules
  作者：Jian-Sen Li、Yun-Hua Fan、Yi Zhang、Luis A. Marky、Barry Gold

  DOI：10.1021/ja028033x

  日期：2003.2.1

  The modeling, synthesis, and characterization of oligomers containing 2-aminoquinazolin-5-yl 2'-deoxynucleotide residues are reported. The 2-arninoquinazoline residues sequence specifically bind via Hoogsteen base pairing as a third strand in the center of the major groove at TA base pair Watson-Crick duplex sequences. Evidence for the formation of a sequence specific three-stranded structure is based on thermal denaturation UV-vis and fluorescence studies. The novel 2-aminoquinazoline C-nucleoticle is a component of a system designed to overcome the homopurine requirement for triple helix structures.